


The Gift Of Dean Winchester's Submission

by joinallthefandoms



Category: Supernatural
Genre: Alternate Universe, Dean doesn't get out of hell, Demon!Dean, Hell, M/M, Pain, Submission, Torture, Violence, this is how dean becomes a demon
Language: English
Status: Completed
Published: 2014-08-03
Updated: 2014-08-15
Packaged: 2018-02-11 13:55:25
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 6
Words: 4,958
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2070822
Author URL: https://archiveofourown.org/users/joinallthefandoms/pseuds/joinallthefandoms
Summary: <blockquote class="userstuff">
              <p>Alastair has had Dean Winchester in his clutches for 30 years. His torture has been exquisite, if he does say so himself. He has employed all of his greatest techniques and yet, the man has not broken. Alastair thinks that Deano will last as long as his Daddy, but alas, he is granted a gift: The gift of Dean Winchester's submission.</p>
            </blockquote>





	1. Prologue

It had taken three months to get Dean Winchester to scream. 

It took another five years for him to beg. 

But to Alastair, these were just consolation prizes, little blue ribbons in comparison to the big trophy he was pursuing. You see, Dean Winchester took after his dear old daddy. He was intransigent, arrogant, and stubborn. The man held out for thirty years when most souls take their first offer to get off the rack. Of course, Deano was quite the requested client. Hordes of demons would gather in their time off to watch Alastair work his craft. They had all learned to be keen on the sound of Dean's screams; they were the most entertaining of any soul that had ever entered Hell. It took some work and a lot of patience, but when Dean screamed, ugh, it was like  _sex_ to Alastair. Deep, throaty, and weighted with the burden of decades of torture, Dean Winchester's screams were the equivalent to the angels' song in Heaven. 

All of the torturers had gotten their turn with Dean, and these were like little vacations for the poor, depraved man. None knew how to properly carve the flesh from someone's bones or where to stick the knife when it had entered an eye socket or where the most sensitive parts of the body were. Everyone goes for the genitals, the nipples, the eyes, but none had the creativity Alastair did. He appreciated the little things; how a simple cut under the arm could cause irritable pain that can eventually drive a person mad, or how useless a person is without their toes and fingers, or that not all pain is physical. 

Alastair learned very quickly exactly how to make Dean writhe (shallow stabbings) , how to make him scream (putting pointy things in holes they oughtn't be), and, best of all, how to make him cry (transform one's self into the image of Sam, John, or Mary Winchester and look him in the eye as you torture him).  Alastair and Dean, in the most perverse ways, were joined as one. Alastair felt incomplete without Dean, and Dean was forced to depend on Alastair's reliability. He was a demon, sure, but he was always straight with Dean. He was a dick, but he was an honest one, and that counted for something in Hell. 

After 20 years, Alastair thought to himself  _he's like his daddy. He's going to hold out on me for another hundred years._ But then, he noticed a change in the man. It was shown in the way that he slowly lost his venom, the way that his snarky comebacks were lackluster after a particularly long day of torture.

Year 20 

"Dean, do you want off the rack?" Alastair asks. 

"Alastair, do you want to go fuck yourself?" Dean retorts with venom in his voice.

Year 22

"Dean, do you want off the rack?" Alastair asks. 

"I'll take a rain check, babe," Dean's voice is hoarse and cracks as he replies with a slight grin on his bloodied face.

Year 24

"Dean, do you want off the rack?" Alastair asks.

"No," Dean wheezes, holding his intestines in with his hand.

Year 26

"Dean, do you want off the rack?" Alastair asks.

Dean can only shake his head

Year 28

"Dean, do you want off the rack?" Alastair asks.

"No," he whispers. 

 

 


	2. Wait, Seriously?

"Dean, do you want off the rack?" Alastair surveys his broken toy. Dean's head is hanging and his chest heaves as he struggles for every breath. Today was one of Alastair's best days; Dean had screamed, begged, cried... it was  _beautiful._  

"Yes," Dean croaks. He's trembling and his voice is so broken and small that Alastair barely hears him. When he does, however, it takes all his composure not to jump for joy. He has successfully broken the unbreakable man. He thinks he should be given a raise. 

"I want off the damn rack, Alastair," Dean's words are harsh, but no conviction stands behind them. He can't muster the strength to be brash. 

"Manners, Deano. Have I taught you nothing all these years?" Alastair is relishing in this moment. He can't help but be smug and condescending, he wants to see how his boy reacts. 

"Please," Dean coughs and the floor is peppered with drops of blood and saliva. "Please, sir." The 'sir' is something he was taught long, long ago. It's a lesson you remember when the word was carved into your chest with a blade that's been lying in a bed of hot coals. He still has that scar. 

"Only because you've been such a good boy, Deano," Alastair begins removing Dean from the rack. The hooks in his shoulders are hard to remove, seeing as they've been in there for thirty years. Dean screams as he physically pulled limb from limb to get off the damned thing. Once he is off, he stands before Alastair on shaky legs. Alastair places a hand on Dean's forehead and within an instant, all his wounds are gone. The dozens of scars have faded and he's no longer in pain. Dean could almost cry in relief, but he refrains. He's about to inquire about what he's supposed to do and where he'll find the souls he'll be torturing when Alastair grabs him by the hair and forces him to his knees. 

"Ah, ah, ah," he scolds. "We need to set some ground rules before I show you around, Kiddo." Dean gulps and nods, ignoring the burning in his scalp from Alstair's far-too-tight grip on his short hair. 

"Rule 1, you will refer to me as Master, and with deference and respect. You will never talk back, nor will you even speak unless spoken to." Dean's pride (or whatever was left of it) shrinks into a little 50 pound ball that weighs in his gut. Humiliation burns in his throat as Alastair shakes him slightly to get him to pay attention. 

"Rule 2, you do as I say, and only as I say. If you are approached by a demon, you are allowed to say no to their requests or demands. You follow my command only, and I'll make that known throughout all of Hell. And, the second you even think to disobey me, I'll have your ass back on the rack for another couple decades."

"Rule 3, the second you stop torturing souls, you go back on the rack for a year minimum. There are no days off, there are no breaks, there is only the rack, and whoever has been placed upon it. Is all of this understood?" Dean nods, but gasps as Alastair thrusts his head backward by the hair so he is looking directly up at him. 

"Yes, Master," Dean grunts, feeling two or three follicles being ripped out of his head. Alastair releases his harsh grip and gestures for Dean to stand up. 

"Follow me," he commands.


	3. Chapter 3

"First time, Deano," Alastair said, way too excited about the whole ordeal. "I'll stay around just this once for moral support. After twenty-four hours, if she hasn't broken, you'll have to take my torture 101 class. But, if you can break her in that amount of time, you can move on to the next soul."  _What a great reward for my efforts_ , Dean thought his sarcastic comment rather than speak it aloud, lest he anger his Master and be brought back to the rack. He approached the woman and tried to avoid meeting her eyes as he chooses a knife at random.  The handle felt familiar and vaguely home-y in his hand as he gripped it tightly. His knuckles were white as he made his first deep cut in the soft flesh of her belly. She screamed the most dreadful scream, but Dean fought to remain stoic. If he got emotional or allowed his empathy to control his head, he would push her off the rack and demand that he take her place. This was Hell. He needed to control his instinct to always sacrifice himself if he was going to survive. 

Two hours later and the poor woman is begging to die.  _What did she do to end up here_ ? Dean wondered. He had seen a lot of shit in Hell, a lot of rotten, twisted souls. But this woman didn't seem to possess the evil Dean had witnessed. Nevertheless, he bared his teeth and kept pushing the bile down as he began to drown in her dreadful screams. _She's here for a reason,_ he reminds himself.  _I may not know why, but people don't just randomly end up in Hell._

Another fiery knife through her breast. Another needle carefully piercing her eardrums. Another scream and another bitter accusation. Another round of begging. Dean's shoes are sodden with the woman's spilled blood and his knife was growing heavy in hand. Alastair stood by, watching eagerly as his student mercilessly drove nails through the bitch's feet. 

"Twenty four-hours, Deano. Make the offer," Alastair waved a nonchalant hand at his pupil. Dean nodded solemnly and turned back to his first victim, fighting to remain stoic and strong as he faced her. 

"Here's how this is gonna work, sweetheart," Dean's voice was heavy with a cruelty he didn't know he possessed. "I let you off the rack if you agree to torture souls. Do what I do, day in and day out, and you don't end up a carved piece of meat. Refuse, and give every damn evil thing in this place the opportunity to sink its claws into you." Dean tossed his bloodied knife down onto the tray, which was now covered with strewn objects of torture. Dean forced himself to look the bitch in the eye as she struggled for words, as she struggled for breath. 

"O-kay," she wheezed, barely having considered refusing the offer. Dean wanted to yell at her for not putting up more a fight, for not being strong enough to sacrifice herself for another, but then he remembered that not everyone can be a Winchester. Not everyone is raised to be a soldier. 

Dean nodded and began moving her off the rack, taking more care to be gentle than he should have. Alastair narrowed his eyes in suspicion as his student gingerly took the woman's shoulder in hand and meticulously began to peel her off the hook. Once she had gotten off, Alastair repaired her wounds and sent her down the hall to begin her own torturing. She went without complaint. 

"Want to tell me what that was, boy?" Alastair crossed his arms like a frustrated teacher. Which, well, he kind of was. 

"What?" Dean's voice was gruff and accusatory as he turned around to face Alastair, having just put away the last of his knives. The elder demon's eyes flashed back and he stepped forward with alarming speed, gripping Dean's throat in his hand. Dean's fingernails scratched at Alastair's hands, but to no avail. He began losing oxygen quickly. 

"Listen to me, kid," Alastair threatened. "I can put you back on the rack just as quickly as I took you off. There are a lot of people like me that never got their turn to play with you, and I'd love to indulge them."

Dean frantically shook his head, fear drowning his evergreen eyes in a shroud of darkness and despair. Tears began forming as the pressure on his windpipe increased and he began seeing stars. Alastair released him and Dean fell to his knees, gasping and wheezing. 

"I'm sorry, Master, I'm sorry," Dean genuflected, barely able to choke out the words. His fear of the rack had since overgrown his pride, and he would be damned (literally) if he would be so haughty as to not grovel in front of his  _Master_. He was not going back on that rack, ever. Not for a stupid dame, not for Sammy, not for anyone. He had to survive, one way or another.

"You're lucky it was I you got assigned to and not Crowley," Alastair said. "Oh, the fun he would have with you."

"Yes, Master," Dean said. He had since regained his breath but he didn't dare rise from his knees. 

"We're going to move on to the next soul. If I see the slightest bit of hesitation, I will-. Well, best to leave that to your imagination." 


	4. Chapter 4

**Notes for the Chapter:**

> This chapter is hella short I'm sorry but there will be a better one once I just get my shit together.

Alastair had Dean wait on his knees like that for hours, he himself sitting comfortably in a chair that had been brought by a lesser black-eyed bastard. Dean kept his head bowed, his eyes focused on a single crack in the floor, and his hands behind his back.  _I'm not going to move,_ he told himself over and over again. The stone floor and minute pebbles were irritating, to say the very least, but he persevered nevertheless. Alastair was kind of like a dinosaur in that, if you didn't make drastic movements, he would not attack. Dean dared not breathe loudly for fear of drawing his attention. The demon himself was deep in thought, considering the many possibilities, the amount of opportunities that would be made available once his boy was in line. Dean Winchester was a good soldier, it was embedded deep into his being. Alastair had a thought of such evil proportions that he grinned and chuckled, breaking the tense silence that had pervaded the torture room. Dean jerked up, startled by the sudden laughter erupting from the demon. That was never good. Alastair stood up just as suddenly, opening the door and starting out into the hallway. He paused for a second as he turned over his shoulder and looked at Dean. 

"Stay," he commanded. Dean nodded in acquiescence, much too afraid that his voice would fail him to actually vocalize his obedience. Alastair left without another word, slamming the door behind him. Dean, once he was sure that the demon wasn't just waiting outside, stretched all his limbs. The cracking of his spine was satisfying, as was the cracking of his neck, knuckles, legs, and ankles. He stood for the first time in what seemed to him like days. People in Hell don't need food or water, and they can die as many times as their torturer wishes, so Dean was not threatened (but nevertheless irritated) by the dryness of his throat. He shook the deadness from his legs and arms as he strolled around the torture room. All in all, it was practically the same size as one of the many motel rooms he had seen in his day, so not very large. Hooks and chains hung from the ceiling as well as the walls, as did knives, needles, branding equipment, belts, hammers, bone saws, and various other implements of torture. The rack, being empty, was four large hooks upon which the victim was situated. Dean gave an involuntary shudder as his hand passed over the cool metal, reminding him of his own years on the damned thing. He longed to leave Hell, as he had since the day he arrived, but he tried not to think about it very often. Nostalgia was possibly the worst self-inflicted torture in Hell. Memories of one's life only served to make one angry and depressed, so Dean often suppressed his urges to indulge the side of his brain that longed to remind him of Sammy.  

Dean was left on his own in the room for about an hour. During that time, he used one of the sharper knives to trim and clean his fingernails, sang at least one song from every album he had in the Impala, and wallowed in self-pity. When Alastair returned, Dean was idly throwing knives at the leather chair left in the demon's hasty exit. When he entered, however, Dean ceased immediately and averted his eyes from the door in spite of his curiosity. Alastair wore a most suspicious smirk on his face as he led two other demons into the room. Except, one of them wasn't a demon...

"Dad," Dean gasped. 


	5. Chapter 5

**Notes for the Chapter:**

> I'm so sorry it took me so long to update, I have a lot going on right now and I couldn't find the time.

John Winchester raised his head expecting to find Alastair or Crowley, his most frequent torturers, but instead found his oldest son. To say that he was shocked is an understatement.

"Dean? What are you doing in Hell?" John demanded.

"It's a long story, Dad," Dean's cheeks burned under his father's unrelentingly stern gaze. It was like he was 7 again and he had just spilled his milkshake all over the console of the Impala.

 

"Where's Sammy?" John's voice was so much more concerned when he inquired about Sam that Dean found himself disappointed. He had always known that Sam was the favorite, that his attempts to impress his father were pointless and stupid and needy, but even now he couldn't help but seek his approval. To hear his Dad be more concerned about Sam than he was his eldest son... it took just a little bit of the weight of what Dean was about to do off his shoulders.

"He's topside," Dean explained. "He's fine." He hated himself for being upset when he saw John sigh and become visibly relieved by that news. Dean wanted to scream in his face  _I'm fine too, thanks! Just been in Hell for thirty years, you dick._ But of course, he refrained. He held his tongue like he was trained to do. 

"We're not here to chat, Deano," Alastair reminded him, the metaphorical devil sitting atop his shoulder. Dean started toward the rack and the tray of instruments that awaited him, but found that he couldn't take his eyes off his dad. John's eyes, which had always possessed a certain maniacal spark, were so devoid of emotion and so apathetic that Dean was drowning in the hopelessness of it all. He started reaching for a knife but John's words stopped him in his tracks.

"What the Hell do you think you're doing, Dean?" John's "angry voice" made Dean, a grown man with thousands of kills under his belt, want to run and hide behind the Motel and cry. His face lightened in understanding and then darkened a second later. "You got off the rack." It was an accusation, not a question. 

"Yeah, I got off the fucking rack!" Dean slammed the knife back onto the tray and turned to face his father. "I got off the damn rack after 30 years of torture, Dad!" 

"You're a coward!" John exclaimed, pulling at the chains binding him. His apathetic eyes had regained that spark of anger Dean had always known to fear. The funny thing was, though, he wasn't afraid anymore. He was...  _excited._

"And that makes you what, exactly?" Dean asked. "Do you want a fucking trophy for lasting longer than me, huh Dad? Call me a coward if you want, but I'm the one holding the knife," Dean growled. Not leaving himself room for second thoughts or empathy, Dean took a harsh grip on the blade and plunged it deep between two of his dad's ribs. John's scream didn't make him feel as guilty as it should have. 

"Sammy would have lasted for an eternity," John growled. "You know why, Dean? Because you're the weak one. You always have been."

Dean employed every technique Alastair had ever used on him. His guilt and sympathy had gone straight out the window. They were quickly replaced by anger, unquenchable rage that only grew stronger with every cut. John continued to yell insults and obscenities at him, but Dean paid them no mind. He was so focused on the canvas in front of him, he had Alastair heal John three times just so he could start over. Days and days went on and Dean didn't tire for a second. Some sort of sadistic pleasure came as a reward for him every time he made his father scream. As he worked away, those horrible memories that he had shoved into the darkest recesses of his brain came back. 

_A twelve-year-old Dean is gasping for breath as the Wendigo stands above him and roars. His vision is darkening quickly and the blood loss will soon drive him into unconsciousness, but more people will die if he can't gank this thing. He, in a final act of desperation, reaches for the flamethrower and sets it ablaze. He smirks slightly as he hears the Wendigo scream and just fades into unconsciousness as it shrivels up into nothing. When he wakes up, the gaping wound on his side is haphazardly patched up with gauze. He is lying in the back of the Impala, with Dad in front, holding that bottle he always seems to have at the ready. Dean hates that bottle._

_"You got yourself wounded," John slurs his speech, taking another big gulp from the bottle. Dean searches frantically for his shirt in the back of the car and slips the blood-sodden garment over his head without complaint._

_"y-yes, sir." He tells himself that he stutters out of shock from the wound because there's no way he's scared of anything, least of all his father._

_"I had to save your ass and carry you back here, boy," John says, turning to look at Dean with glazed eyes. Dean's eyes dart to the other bottles strewn on the floor and silently says a prayer even though he knows angels aren't real because Dad says they aren't/_

_"I'm sorry, sir," Dean says, wincing as John puts the bottle down. He begins taking off his belt._

_"You'll be sorry," John growls. "Get out of the car and take off your damn shirt."_

_"Yes, sir," Dean whispers. He gets out of the car and Dad beats him until he passes out again. When he wakes up, they're back at the hotel and Sammy is holding a wet cloth to the bleeding marks on his back._

Dean doesn't force himself to swallow his anger and resentment for his father this time. Instead, he lets the fiery poker do the talking as he spells out the word "coward" on his father's chest. He grins as John wails with every new stroke of his masterful paintbrush. 

_A fifteen-year-old Dean and eleven-year-old Sam push the Impala back into the motel parking lot._

_"Dad's going to kill me for wrecking the car," Sam says, fear evident in his eyes and shaking hands. Dean forces him to stop and pulls him into a rare but nevertheless compassionate hug. Sam hugs back, wrapping his thin arms around his brother's muscled abdomen. Even though he knew he was right and that his Dad was going to go crazy for Dean even letting him in the driver's seat, Dean's hug comforts him. They see their room door open as they give the Impala a final push into a parking space. Dad is fuming._

_"What the hell is going on, Dean?" John's venomous words are, of course, directed at Dean. Sammy opens his mouth to explain, but Dean pinches him on the back discreetly._

_"It was my fault, Dad," Dean confesses. Sam is about to refute him but Dean starts tapping morse code onto his back._ _Don't, let me handle it._

_"Sam could have gotten hurt, Dean!" John exclaims, pointing to a spot just right of Sam. He's drunk, Dean taps on Sam's back. Go inside._ _Sam obeys his brother and ducks into the room where he discreetly watches from the window. He watches as John screams and Dean just takes it. Dean bows his head in false shame as John berates him and he barely reacts when a harsh slap comes out of nowhere. Sam knows that if he had just taken the blame for what he did, Dad wouldn't beat him. Dad never beat him, only Dean._

Dean turned to Alastair after nearly an entire week of endless, relentless torture. Blood stains his hands, his fingernails, his hair, his shirt, his shoes, just bathing him in blood. He is not tired, nor has he little passion left for what he's been doing. He's simply run out of techniques. Maybe he will take that Torture 101 Class...

"Good enough, Master?" Dean asks, wiping his bloody hands on his equally bloody jeans. Alastair chuckles and ruffles Dean's hair the way Bobby did when he was a kid. The weird thing is, Dean finds it kind of comforting. 

"Brilliant, my boy," he says. "Take a day off, Kiddo, and meet me back here the day after next. There's a lot to learn."

"Thank you, Master," Dean bows his head and walks out of the room, feeling much better leaving than he did entering. Maybe he could survive here. 


	6. Epilogue/ Bonus Chapter

Dean Winchester was never placed on the rack again. 

It had taken 30 years to break him and just two torturings to motivate him. After seeing his father on the rack the first time, Dean saw him by his own request another dozen or so times. it was during those sessions that John most strongly considered taking the deal offered to him. 

After 40 years, Dean had become as good a torturer as Alastair. His name had gone from being tossed about and mocked amongst snickering demons to being whispered in reverence. Demons respected him nearly as much as they did Alastair and Crowley, even if he himself was not a demon... yet. 

100 years of exemplary torturing later and Dean was allowed an audience with Crowley. 

_"Are you ready, kid?" Alastair asked, placing a comfortable and reassuring hand on Dean's shoulder._

_"Yes, sir," Dean replied. They had since passed the phase of Dean's humiliation that Alastair no longer cared if he was referred to as Master. They were so familiar and comfortable with each other that Dean no longer feared Alastair punishing him. He had gone from fearing his torturer to respecting and caring for him. Sometimes they shared a whiskey or two that Crowley somehow got delivered into Hell regularly. The King's got to have his pick-me-ups._

_Dean walked through the door and kneeled willingly before the King of Hell._

_"Hello, Dean," Crowley purred. His voice was unexpectedly gruff and British. "There's no need for the formalities. We're just here to chat." Dean looked up in surprise, unaware that he and the King of Hell were on such friendly terms._

_"Have a drink," Crowley offered, waving his hand at the table set between two leather armchairs. Dean poured himself a generous amount of whiskey and sat hesitantly in one of the chairs._

_"I've heard a lot about you," Crowley said, pouring himself a drink and proceeding to sit down in the chair facing Dean's._

_"And I, you, sir," Dean replied, his snark and sarcasm still strong inside him after 100 years. It had taken a few years after getting off the rack, but he had regained some semblance of his old self, what with his wit and self-loathing. The self-loathing was lost after another couple decades, only to be replaced by sadistic pleasure._

_Crowley chuckled. "So, riddle me this, Winchester," he said. "Most souls turn into demons only a few months after accepting their deal._  (A/N: I have no idea if this is accurate or not. Just go with it.) _What makes you so special that you're able to hold on to humanity for an entire century?"_

_"I'm just too cuddly and humane, I suppose, sir," Dean cracked, taking a large gulp of his whiskey and whistling as the amber fire blazed a trail down his throat and sat in the pit of his stomach. Good whiskey, he thought._

_At this, Crowley laughed. "Well, here's to our humanity, Dean." He raised his glass, and Dean tapped it._

Dean and Crowley had gotten on famously, bonding over their love for alcohol and sarcastic humor. Crowley had, after just a few decades, become something of a replacement Sam. In fact, Dean had barely thought of Sam since he had tortured John. At first it was just too painful for him to think of home while he was stuck in Hell, but then he had just become so engrossed in his work that he had kind of forgotten about him. Dean had just marked his 200th year in Hell when he received the news that Sammy had died. 200 years was roughly 5 years on the surface, so Dean was more than a little mad when he found out that his brother had gone and gotten himself killed by a vampire just 5 fucking years after Dean had sacrificed himself for him. 

It was Dean's anger at Sam that caused him to lose his last shred of humanity and become a demon. The only thing that had kept him a human thus far, the only thing that redeemed his actions in Hell, was that he had done it all for Sammy. When Dean heard the news, he was not upset, he was not mourning, he was angry that his sacrifice had been wasted. He yelled at Sammy up in Heaven and damned him and screamed for all of Hell to hear that he wished the roles were reversed. He wished that he had just let Sammy stay dead. He would've been better off, he said, without his burden of a brother. 

Dean woke up the next day with black eyes and a thirst for blood. 

Centuries passed and Dean became Crowley's right-hand man, his best friend, and his willing servant. Together, they hunted humans up on the surface, tortured souls, and drank way too much whiskey. 

There was no savior Castiel, nor would there ever be. Dean Winchester had become too broken to fix, so the angels didn't even try. Dean Winchester was a hardworking soldier, then a sacrificial brother, a condemned warrior, a depraved soul, and last of all. a demon. 

He had become the very thing he had always hunted, and all because he had given away the gift of his own submission. 

**Notes for the Chapter:**

> Not a happy ending, I'm not sorry.  
> I am sorry, however, that the ending is kind of awkward, i just didn't know how to wrap it all up.


End file.
